This invention relates to sulfamoyl chlorides which are useful as intermediates for preparing sulfamides and pyrrole sulfonamides which are useful as agricultural chemicals and particularly as herbicides.
The sulfamides of this invention are compounds of the formula ##STR1## wherein R.sub.10 and R.sub.9 are as defined below.
The pyrrole compounds are disclosed in co-pending U.S. application Ser. No. 244,172, filed Mar. 25, 1981 and have the general formulae: ##STR2## wherein
R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, NO.sub.2, CN, C(O)CCl.sub.3, SO.sub.2 R.sub.11, C(O)R.sub.5, or CO.sub.2 H;
R.sub.2 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, Cl or Br;
R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, cyanoethyl, C.sub.5 -C.sub.6 cycloalkyl, benzyl, phenyl substituted with Cl or NO.sub.2, or C(O)R.sub.6 ;
R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, or NR.sub.7 R.sub.8 ;
R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.2 alkyl;
R.sub.9 is H, CH.sub.3 or OCH.sub.3 ;
R.sub.11 is C.sub.1 -C.sub.4 alkyl;
R.sub.10 is ##STR3##
X is CH.sub.3 or OCH.sub.3 ;
Y is H, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3, Cl, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3 or CF.sub.3 ;
Y.sup.1 is H, CH.sub.3, OCH.sub.3, Cl or OCH.sub.2 CH.sub.3 ; and
Z is CH, N, CCH.sub.3 CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl, CCl, CBr or CF; and their agriculturally suitable salts;
provided that
(1) when R.sub.4 is C(O)R.sub.6, t-butyl or phenyl substituted with Cl or NO.sub.2, then R.sub.1 is H or C.sub.1 -C.sub.4 alkyl and R.sub.1, R.sub.2 and R.sub.3 cannot be s-butyl or isopropyl;
(2) R.sub.1, R.sub.2, R.sub.3 and R.sub.11 cannot be t-butyl;
(3) in Formula Ia, when R.sub.1 is NO.sub.2, then R.sub.1 cannot be in the 5-position;
(4) in Formula Ia, when R.sub.1 is not in the 5-position, R.sub.2 and R.sub.3 are other than H, and R.sub.1 must be other than H unless both R.sub.2 and R.sub.3 are H;
(5) in Formula Ia, R.sub.3 cannot be Cl or Br;
(6) in Formula Ib, R.sub.1 cannot be C(O)CCl.sub.3 ; and
(7) in Formula Ib, when R.sub.3 is Cl or Br, then R.sub.3 is in the 3-position and R.sub.1 is in the 5-position and R.sub.1 cannot be H or C.sub.1 -C.sub.4 alkyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs such as soybeans, barley wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such crops by killing or inhibiting the growth of undesired vegetation, with herbicidal compounds such as those described above, is one way of improving this efficiency.
Useful intermediates, such as those of the instant invention, facilitate the production of the desired herbicidal compounds.
German Pat. No. 2,439,087 discloses the following compound: ##STR4##